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Green synthesis of novel spiropyrazoline-indolinones in neutral deep eutectic solvents and DFT studies.

ABSTRACT: Novel spiropyrazoline-indolinones (4a-t) have been synthesized successfully in neutral deep eutectic solvents by reacting 5-Cl/Br-isatin (1a-b) with aromatic ketones (2a-b) and a variety of substituted hydrazines (3a-e) in good to excellent yields. This eco-friendly straightforward synthetic protocol discloses good functional group compatibility. The conventional synthetic approach was compared with the greener route of microwave-assisted synthesis of spiropyrazolines using ethanol. This approach utilized mild reaction conditions which furnished high yields in short reaction time employing one pot two-step multicomponent. All new compounds were structurally confirmed by detailed spectroscopic analysis and density functional theory calculations. This method provides efficient access to spiropyrazole derivatives using biodegradable and green solvent.

SUBMITTER: Sadiq Z

PROVIDER: S-EPMC10788502 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Green synthesis of novel spiropyrazoline-indolinones in neutral deep eutectic solvents and DFT studies.

Sadiq Zubi Z Ghani Ambreen A Hashmi Muhammad A MA Dahshan A A Shahnaz Al-Mijalli Samiah H SH Iqbal Munawar M Hussain Erum A EA

Heliyon 20231220 1

Novel spiropyrazoline-indolinones (4a-t) have been synthesized successfully in neutral deep eutectic solvents by reacting 5-Cl/Br-isatin (1a-b) with aromatic ketones (2a-b) and a variety of substituted hydrazines (3a-e) in good to excellent yields. This eco-friendly straightforward synthetic protocol discloses good functional group compatibility. The conventional synthetic approach was compared with the greener route of microwave-assisted synthesis of spiropyrazolines ...[more]

PMID: 38226241

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Project description:The sustainable extraction of natural compounds has recently attracted significant attention. The extraction of high-quality natural vanillin in active form is crucial for its efficient use in various industries, but conventional solvents are not suitable for this purpose. The flammability, volatility, and toxicity of organic solvents can harm extraction personnel, and their waste liquid can cause environmental pollution. Natural deep eutectic solvents (NADES) are cost-effective, environmentally friendly, biodegradable, and non-toxic organic alternative to conventional solvents. In this study, 20 different NADES were tested for the sustainable extraction of natural vanillin. Among these, a DES system composed of choline chloride: 1,4-butanediol: lactic acid exhibited the highest extraction rate (15.9 mg/g). Employing response surface methodology (RSM), optimal extraction conditions were determined, yielding a vanillin content 18.5 mg/g with water content of 33.9%, extraction temperature of 64.6°C, extraction time of 32.3 min, and a solid-liquid ratio of 44.9 mg/mL. Subsequently, the optimized NADES system was then assessed for reusability in extracting vanillin from vanilla pods and kraft lignin over three cycles, retaining 43% of its extraction efficiency and demonstrating potential for waste reduction. Purification of vanillin was achieved through chromatography using a non-polar resin SP700, with ethanol as a desorption eluent and a feed solution pH of 4.0, resulting in the highest vanillin purity. HPLC and GC-MS analyses confirmed purity, while antioxidant activity assays (DPPH and ABTS) showcased significant antioxidant activity of the purified vanillin. Moreover, vanillin exhibited notable antimicrobial activity against a panel of food-borne bacteria. This study introduces an environmentally friendly approach to vanillin extraction highlights using NADES, emphasizing the potential for producing high-quality bioactive vanillin with reduced environmental impact. The applicability of NADES systems extends beyond vanillin, offering a versatile method for extracting diverse natural compounds.

Dataset Information

Green synthesis of novel spiropyrazoline-indolinones in neutral deep eutectic solvents and DFT studies.

Publications

Green synthesis of novel spiropyrazoline-indolinones in neutral deep eutectic solvents and DFT studies.

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